I didn't think people would come out to W. Mass, so the first place that popped into my head was:
Stromberg's in Salem, MA, on Bridge St. (Rte. 1A). If you like seafood, it's fantastic...and has an excellent view of the inlet and salt-marshes. My ex and I used to go there quite a lot when we lived in Newburyport. Try the fish chowder!
For more, I had to jog my memory, so I asked my mother, who goes out with her friends and their "Supper Club" almost every week. These were just a few of their favorites:
The Whistling Swan in Sturbridge is very good, but incredibly overpriced.
Judi's, in Amherst is also excellent.
For great Chinese food, try Amherst Chinese Food - (Mandarin).
I can't believe more than one person (including the supper club) recommended The Salem Cross (W.Brookfield) - ugh! I've been there for private dinners and business functions: BLAND!!!
If you like Cajun and other blackened food, check out The Eastside Grill in Northampton. Spoleto's is quite good.
Also in Northampton, Union Station (formerly "The Depot"), 125 Pleasant Street, is not only very good, but atmospheric--it's in a restored, early 20th Century train station (very art-deco). Every so often, a train will thunder past!
There are just too many in that area to name.
If you're going further out into the country, the Whately Inn, off Routes 5+10 in Whately Center is excellent but quite expensive.
For very solid fare, in a casual setting, "Wolfie's" in South Deerfield Center (just north of Whately, is a good choice.
The same is true of The Four Leaf Clover Restaurant at the Junction of Rts. 5 & 10 and close to I-91, in the Center of Bernardston.
If you want the Barbecue equivalent of rustic Woodman's in Ipswich (seafood), try "Bub's Barbecue" on route 116 in Sunderland, just a few miles north of UMass/Amhert.
There are also many fine restaurants in Brattleboro, VT, but I haven't been there for so long, I don't know which ones still exist!
For a great eating vacation, start in Amhert, then head over to Northampton, then work your way along Rts. 5 & 10 North, to Brattleboro! Then head to the gym....
